How to Jailbreak iOS 14.1~14.4.2 Using Checkra1n on iPhone or iPad

Here’s how to use Checkra1n to jailbreak iOS 14.1~14.4.2 on a handful of older Apple devices.

Jailbreak Compatible Devices:

iPhone 6s, 6s Plus, and SE
iPad 5th generation
iPad Air 2
iPad mini 4
iPad Pro 1st generation

Preparations Before Jailbreaking:

Delete any iOS 14.1~14.4.2 OTA update file from Settings > Storage and reboot your device before attempting to jailbreak it.
A computer running macOS.
The latest version of iTunes installed if using a Mac running anything prior to macOS Catalina.
Make sure to create a backup of all important data on your device before proceeding with the jailbreaking steps.

Processes of Checkra1n Jailbreak

Step 1:

Download the Checkra1n app for macOS from here. Proceed to install it by opening the DMG and dragging the app to the Applications folder.

Step 2:

If your Mac lets you know that it can’t open the app or that it can’t be trusted, follow the simple steps below to resolve the problem. Or, if everything opens as you would expect and no errors are thrown, then move to Step 3:

Head into the System Preferences app and select the Security & Privacy option.
Select Open Anyway followed by Open and enter your administrator password when prompted.
Try to run the Checkra1n app again and you shouldn’t have any issues. Just another hurdle that Apple wants you to overcome.

Step 3:

Run Checkra1n and then move into the Checkra1n Options and check the Allow untested iOS/iPadOS/tvOS versions option. Select Back.

Step 4:

With Checkra1n still running, connect your device via a Lightning cable and then click the Start button and select OK.

Step 5:

Select Next when it appears and then follows the instructions that are given directly in the Checkra1n app. This will involve putting your device into the required DFU Mode needed to continue.

Step 6:

As soon as DFU Mode is activated and detected, Checkra1n will detect the device and start the jailbreak process. This will involve your iPhone or iPad rebooting a few times so keep in mind that this is normal and a required part of the process.